Ossining Holidays from AU$2,259

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Your Ossining Holiday

With one of our holiday packages to Ossining, you'll find countless opportunities for fun and relaxation. There's tons to experience, including its rich history and spectacular views. Make your trip to Ossining even more fun by going sightseeing. Van Cortlandt Manor, Sleepy Hollow Cemetery and Tarrytown Music Hall are among the popular attractions worth exploring. Don't delay your visit to this city any longer. Your ultimate Ossining holiday is only a few clicks away with Expedia.

The Latest Ossining Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
Save 100% on your flight
per person
18 Oct - 24 Oct
found 14 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.6/10 Exceptional! (8 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.

Reviewed on 25 Jun. 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
6 Oct - 11 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (2,727 reviews)
Our stay was amazing. Highly recommend. We'll be staying again.

Reviewed on 31 Jul. 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
6 Oct - 11 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (3,398 reviews)
The property we great, staff was very friendly. However the driver we had for the car service was not the best.

Reviewed on 2 Aug. 2025

The Renwick

The Renwick

4 out of 5
Manhattan
per person
11 Oct - 18 Oct
found 2 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (1,893 reviews)
I would say pictures are not very representative of the hotel. The rooms are pretty spacious for nyc but it is not modern, not perfectly clean and it felt old … not sure it worth the price, you can definitely find a better place. Otherwise the location was great and the staff very friendly.

Reviewed on 30 Jul. 2025

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
per person
6 Oct - 11 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8.4/10 Very Good! (1,385 reviews)
Excellent location and great staff service; property was dated and could use a carpet refresh. Room was comfortable for NYC standards. Good hotel for the price and location

Reviewed on 2 Aug. 2025

Ossining Holiday

Ossining Essential Information

Language
English
Currency
U.S dollars
Closest Airport
LaGuardia Airport (LGA)
Population
25,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Bear Mountain State Park, Franklin D. Roosevelt State Park and Paramount Hudson Valley Theatre

Our pick of the best Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

2 out of 5
1 Old Albany Post Rd, Ossining, NY
The price is AU$428 per night from 4 Aug to 5 Aug
AU$428
4 Aug - 5 Aug
includes taxes & fees
8/10 Very Good! (7 reviews)
"Very unique property. It's a big onsite property like a campus - and they have carved out a hotel area. Very new, well kept buildings and grounds. The location is actually on a long hiking trail with beautiful views. The room wasn't huge but very clean and beautiful floor to ceiling windows. Staff ..."

Reviewed on 30 Jul. 2025

Windrose On Hudson
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
The price is AU$124 per night from 2 Sept to 3 Sept
AU$124
2 Sept - 3 Sept
includes taxes & fees
6/10 (1,980 reviews)
"Good"

Reviewed on 20 Jul. 2025

Armoni Inn & Suites
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is AU$254 per night from 10 Aug to 11 Aug
AU$254
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (1,384 reviews)
Visit stay
"For me it was close to the hospital and the staff at the hotel was friendly and gave me a good suggestions for places to eat."

Reviewed on 29 Jul. 2025

Baymont by Wyndham White Plains - Elmsford
See all 1,204 properties in Ossining
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Ossining

Sing Sing Correctional Facility

After visiting Sing Sing Correctional Facility, make a plan to see the other sights and activities in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

Sing Sing Correctional Facility

Frequently asked questions

How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from AU$2,259 on Expedia. However, how much your holiday to Ossining costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Ossining?
The off-season is the best time to head to Ossining if you're hoping to keep costs down. Another tip for scoring cheap Ossining holiday packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Ossining?
To fully enjoy your Ossining holiday, we recommend staying for 5 days. Divide your time between visiting Teatown Lake Reservation, Kitchawan Preserve and other top attractions, in addition to experiencing neighbourhoods like Town of Mount Pleasant and Pleasantville. If you've got some time to spare, add a tour or day trip to your Ossining holiday itinerary.
Is it worth booking a holiday package to Ossining?
Ossining has everything you need for an unforgettable escape. Get your Ossining holiday off to a flying start by visiting top attractions like Louis Engel Waterfront Park.
How to find the best Ossining package deals?
Use Expedia's handy filters to find some tempting Ossining package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Ossining package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book an Ossining holiday as a package?
You can enjoy significant savings on your Ossining retreat by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Ossining?
If you have your Ossining travel dates locked in, book as early as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Ossining?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Ossining.
  2. Budget wisely: Besides the price of your accommodation, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Ossining.
  3. Set the duration of your trip: Start by listing all the attractions and activities you'd like to get to in Ossining. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your accommodation and airfare: After you've settled on your dates and duration, lock in the ideal Ossining holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.